(2R,3R)-2,3-bis(benzoyloxy)-3-(dimethylcarbamoyl)propanoic acid

• ChemBase ID: 152214
• Molecular Formular: C20H19NO7
• Molecular Mass: 385.36736
• Monoisotopic Mass: 385.11615195
• SMILES: CN(C)C(=O)[C@@H]([C@H](C(=O)O)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• Canonical SMILES: CN(C(=O)[C@@H]([C@H](C(=O)O)OC(=O)c1ccccc1)OC(=O)c1ccccc1)C
• InChI: InChI=1S/C20H19NO7/c1-21(2)17(22)15(27-19(25)13-9-5-3-6-10-13)16(18(23)24)28-20(26)14-11-7-4-8-12-14/h3-12,15-16H,1-2H3,(H,23,24)/t15-,16-/m1/s1
• InChIKey: LINPSOODYGSBAH-HZPDHXFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-bis(benzoyloxy)-3-(dimethylcarbamoyl)propanoic acid
• IUPAC Traditional name: (2R,3R)-2,3-bis(benzoyloxy)-3-(dimethylcarbamoyl)propanoic acid
• Synonyms: (-)-O,O′-Dibenzoyl-L-tartaric acid mono(dimethylamide); (-)-O,O′-二苯甲酰-L-酒石酸单(二甲酰胺)

Database IDs

• CAS Number: 78761-37-2
• PubChem SID: 24860367; 162246359
• PubChem CID: 13932120

CALCULATED PROPERTIES

• Acid pKa: 3.293262
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.61296177
• LogD (pH = 7.4): -0.62531036
• Log P: 2.8022094
• Molar Refractivity: 97.473 cm^3
• Polarizability: 37.93697 Å^3
• Polar Surface Area: 110.21 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 150-152 °C (dec.)
• Optical Rotation: [α]20/D -79±1°, c = 5% in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0%
• Empirical Formula (Hill Notation): C20H19NO7

DETAILS

Sigma Aldrich - 33624

Application
Chiral acid useful for the resolution of amines
Packaging
50 g in poly bottle